Gas chromatographic enantiomer separation on a chiral self-associating selector

被引:15
作者
Betschinger, F [1 ]
Libman, J [1 ]
Shanzer, A [1 ]
机构
[1] WEIZMANN INST SCI,DEPT ORGAN CHEM,IL-76100 REHOVOT,ISRAEL
关键词
enantiomer separation; chiral stationary phases; GC; amino acids; hydroxy acids;
D O I
10.1016/0021-9673(96)00308-1
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A novel chiral stationary phase bearing a tripodal selector is described. In gas chromatography this phase exhibits high enantioselectivity towards derivatized amino acids and moderate capability for the enantiomer separation of derivatized hydroxy acids. Due to a C-3 symmetric arrangement of three N-acyl-valine-tert-butyl amide groups the tripodal selector adopts a hydrogen bonding network involving inter- and intrastrand hydrogen bonds. Thus a conformationally constrained structure is formed which is stable up to 150 degrees C.
引用
收藏
页码:53 / 62
页数:10
相关论文
共 23 条
[11]   CHIRAL POLYSILOXANES FOR RESOLUTION OF OPTICAL-ANTIPODES [J].
FRANK, H ;
GRAEME, JN ;
BAYER, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (05) :363-365
[12]   RAPID GAS-CHROMATOGRAPHIC SEPARATION OF AMINO-ACID ENANTIOMERS WITH A NOVEL CHIRAL STATIONARY PHASE [J].
FRANK, H ;
NICHOLSON, GJ ;
BAYER, E .
JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1977, 15 (05) :174-176
[13]   CHIRAL STATIONARY PHASES FOR CAPILLARY GAS-CHROMATOGRAPHY - TOWARDS HIGHER SELECTIVITY AND STABILITY [J].
FRANK, H .
JOURNAL OF HIGH RESOLUTION CHROMATOGRAPHY & CHROMATOGRAPHY COMMUNICATIONS, 1988, 11 (11) :787-792
[14]   CHIRAL RECOGNITION IN THE RESOLUTION OF ENANTIOMERS BY GLC [J].
KOPPENHOEFER, B ;
BAYER, E .
CHROMATOGRAPHIA, 1984, 19 :123-130
[15]   DIRECT RESOLUTION OF ENANTIOMERS OF 2-HYDROXY AND 3-HYDROXY ACID ALKYL ESTERS BY FUSED-SILICA CAPILLARY GAS-CHROMATOGRAPHY [J].
KOPPENHOEFER, B ;
ALLMENDINGER, H ;
NICHOLSON, GJ ;
BAYER, E .
JOURNAL OF CHROMATOGRAPHY, 1983, 260 (01) :63-73
[16]   BACKBONE MODIFICATION OF CHIRASIL-VAL .2. INTRODUCTION OF A RIGID CYCLOHEXYL SPACER [J].
KOPPENHOEFER, B ;
MUHLECK, U ;
WALSER, M ;
LOHMILLER, K .
JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1995, 33 (05) :217-222
[17]  
KOPPENHOEFER B, 1995, J CHROMATOGR A, V99, P215
[18]  
Koppenhoefer B., 1985, J CHROMATOGR LIB, V32, P1
[19]  
LIBMAN J, 1992, ISRAEL J CHEM, V32, P31
[20]   RECOGNITION OF ENANTIOMERS BY CHIRASIL-VAL AND OLIGOPEPTIDE ANALOGS AS STUDIED BY GAS-PHASE CALORIMETRY AND H-1-NMR SPECTROSCOPY IN SOLUTION [J].
LOHMILLER, K ;
BAYER, E ;
KOPPENHOEFER, B .
JOURNAL OF CHROMATOGRAPHY, 1993, 634 (01) :65-77